- Convenient synthesis of benzoylecgonine ethyl ester, a homolog of cocaine
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Benzoylecgonine reacted with tetramethylethyhlenediamine to form a lipophilic ion pair, which was alkylated in the absence of water. The ethyl ester was readily recrystallized for pharmacological studies.
- Brzezinski,Christian,Lin,Dean,Bosron,Harper
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- Cocaethylene, the in vivo product of cocaine and ethanol, is a narcotic more potent than its precursors
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The molecular conformation and supramolecular architecture of cocaethylene [systematic name: ethyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo- [3.2.1]octane-2-carboxylate], C18H23NO4, have been determined for the first time. Cocaethylene is a narcotic produced in vivo when cocaine and ethanol are administered concomitantly. The intra- and intermolecular features of cocaethylene and its less potent narcotic precursor cocaine are very similar. The only molecular difference is in the conformation of the methyl group of the ethoxycarbonyl group. Similar to cocaine, the carboxylate atoms and the α-C atom are coplanar in cocaethylene, but the methyl C atom of the ethyl group is bent by ca 90° away from this plane in the narcotic reported here. The main supramolecular motif is a one-dimensional chain stabilized by weak C-H.O contacts.
- Da Silva Maia, Angélica Faleiros,Martins, Felipe T.,Da Silva Neto, Leonardo,Alves, Rosemeire Brondi,De Fátim, Angelo
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- 2β-Substituted Analogues of Cocaine. Synthesis and Inhibition of Binding to the Cocaine Receptor
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The potencies of a series of 2β-substituted cocaine analogues to displace -3β-(p-fluorophenyl)tropane-2β-carboxylic acid methyl ester binding in rat striatal membranes demonstrate the requirement for a 2β-substituent with two hydrogen-bond acceptors.The insensitivity of the ester moiety to steric and electronic factors suggests its modification to provide site-specific irreversible ligands.
- Lewin, Anita H.,Gao, Yigong,Abraham, Philip,Boja, John W.,Kuhar, Michael J.,Carroll, F. Ivy
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p. 135 - 140
(2007/10/02)
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